First example of axial selectivity in the nucleophilic addition to (-)-menthone - addition of cyanomethyl lithium

The addition of cyanomethyl lithium to (-)-menthone at -78 degrees C followed by 1.5 h stirring at room temperature and acidic workup produced exclusively the axial addition product, being the first example of preferred axial attack of an organometallic reagent to menthone. In the case of hydrolysis at -78 degrees C after 0.5 h reaction time the equatorial addition product was isolated as the preferably formed isomer. The axial and equatorial cyanomethyl substituted menthol and neomenthol, respectively, were isolated in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.